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EP3242920B1 - Nouveaux additifs pour applications industrielles et pétrolifères - Google Patents

Nouveaux additifs pour applications industrielles et pétrolifères Download PDF

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Publication number
EP3242920B1
EP3242920B1 EP15700192.6A EP15700192A EP3242920B1 EP 3242920 B1 EP3242920 B1 EP 3242920B1 EP 15700192 A EP15700192 A EP 15700192A EP 3242920 B1 EP3242920 B1 EP 3242920B1
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EP
European Patent Office
Prior art keywords
carboxylic acid
derivative
oil
ether carboxylic
lubricant
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Application number
EP15700192.6A
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German (de)
English (en)
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EP3242920A1 (fr
Inventor
Diana MÄKER
Heinz Müller
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Emery Oleochemicals GmbH
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Emery Oleochemicals GmbH
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/18—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/24—Polyethers
    • C10M145/26—Polyoxyalkylenes
    • C10M145/36—Polyoxyalkylenes etherified
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/02—Well-drilling compositions
    • C09K8/03—Specific additives for general use in well-drilling compositions
    • C09K8/035—Organic additives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/02—Well-drilling compositions
    • C09K8/32—Non-aqueous well-drilling compositions, e.g. oil-based
    • C09K8/36—Water-in-oil emulsions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
    • C10M107/34—Polyoxyalkylenes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
    • C09K2208/34—Lubricant additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
    • C10M2209/1085—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/02—Pour-point; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/24—Emulsion properties

Definitions

  • the present invention relates to new ether carboxylic acids as highly temperature stable rheology modifier, viscosifier, lubricant or emulsifier additives in oilfield and industrial applications.
  • the invention relates to an ether carboxylic acid or a derivative thereof obtainable by reacting a branched polyol alkoxylate with a halogen carboxylic acid or a halogen carboxylic acid derivative.
  • Further aspects of the invention relate to a lubricant composition comprising an ether carboxylic acid of the invention and the use of said ether carboxylic acid.
  • Drilling fluids generally contain certain additives.
  • such additives can be a viscosifier, a suspending agent, a dispersant, a thinner, an anti-balling additive, a lubricant, a wetting agent, a seepage control additive, a drilling enhancer, a penetration rate enhancer, a corrosion inhibitor, an acid, a base, a gelling agent and buffers.
  • Drilling fluids can be used in both oilfield applications and also in other industrial settings.
  • a drill bit at the end of a rotating drill string, or at the end of a drill motor is used to penetrate through geologic formations.
  • drilling mud is typically circulated through the drill string, out of the bit, and returned to the surface via the annular space between the drill pipe and the formation.
  • Drilling mud serves numerous functions, including cooling and lubricating the drill string and drill bit, counterbalancing the pressures encountered in the formation using hydrostatic pressure, providing a washing action to remove the formation cuttings from the wellbore, and forming a friction reducing wall cake between the drill string and the wellbore.
  • Drilling fluids for sinking wells in rock and bringing up the rock cuttings are flowable systems which may be assigned to any of the following three classes: purely aqueous drilling fluids, oil-based drilling fluids, which are generally used as so-called invert emulsion fluids, in which the aqueous phase is heterogeneously distributed as a fine dispersion in the continuous oil phase.
  • the third class of known drilling fluids is built up on water-based o/w emulsions, i.e. on liquid systems which contain a heterogeneous, finely disperse oil phase in a continuous aqueous phase.
  • the present invention provides in a first aspect an ether carboxylic acid or a derivative thereof, wherein said ether carboxylic acid is obtainable by reacting
  • a lubricant composition comprising
  • a further aspect of the invention relates to the use of an ether carboxylic acid or a derivative thereof of the invention as a rheology modifier, viscosifier, lubricant or emulsifier.
  • the present invention provides novel ether carboxylic acid and derivatives thereof. It was unexpectedly found that the ether carboxylic acid and derivatives thereof of the invention are useful as viscosifier, lubricant or emulsifier in lubricant compositions.
  • the invention provides ether carboxylic acid or a derivative thereof, wherein said ether carboxylic acid is obtainable by reacting
  • ethers of the invention can be obtained utilizing conventional ether production procedures such as those described in the examples below.
  • the ether carboxylic acid is an aliphatic ether carboxylic acid.
  • the ether carboxylic acid is in a preferred embodiment an aliphatic ether polycarboxylic acid.
  • the ether carboxylic acid is an ether monocarboxylic acid, an ether dicarboxylic acid, an ether tricarboxylic acid, or a mixture thereof.
  • the derivative is selected from the group consisting of a salt of said carboxylic acid, an ester of said carboxylic acid and an amide of said carboxylic acid.
  • said polyol alkoxylate is obtainable by alkoxylating said C18-C54 diol or C18-C54 triol.
  • the polyol is a C26-C42 diol or C39-C54 triol and more preferably a C34-C38 diol or C39-C54 triol.
  • the polyol is a C18-C54 dimer diol or a C18-C54 trimer triol, more preferably a C26-C42 dimer diol or a C39-C54 trimer triol or even more preferably a C34-C38 dimer diol or a C39-C54 trimer triol.
  • said polyol alkoxylate is obtainable by alkoxylating a C36 dimer diol, a C54 trimer triol, or a mixture thereof.
  • Dimer diols and trimer triols are well known in the art. They can be obtained, for example, by dimerizing or trimerizing, respectively, unsaturated fatty acids and then reducing the dimerized or trimerized fatty acid product (e.g. via hydrogenation) to obtain the respective dimer diol or trimer triol. Dimer diols are already known in the prior art (see for example US 20140018333 A1 ).
  • Dimer diols can be produced for example as shown in the following example where a C36 dimer diol is synthesized starting from linoleic acid and oleic acid:
  • the alkoxylated polyol comprises in total at most 50 alkoxy (e.g. ethoxy, propoxy, butyloxy radicals, or a mixture thereof) radicals. In a preferred embodiment, the alkoxylated polyol comprises in total at most 10, 20 or at most 30 alkoxy (e.g. ethoxy, propoxy, butyloxy radicals, or a mixture thereof) radicals. In a preferred embodiment, the polyol is alkoxylated with ethylene oxide and/or propylene oxide. Accordingly, in a preferred embodiment of the ether carboxylic acid or derivative thereof according to the invention said polyol is ethoxylated and/or propoxylated.
  • the polyol is an aliphatic alcohol, optionally comprising a ring structure, or an aromatic alcohol.
  • said polyol has a general formula selected from the following group: and wherein n, o, p, q and r are each individually selected from an integer of between 3 and 12; and ring B can be aromatic or aliphatic.
  • said polyol is an alkyl polyol.
  • said alkyl polyol comprises or consists of the following dimer diol:
  • the ether carboxylic acid of the invention is obtainable by reacting said polyol alkoxylate with said halogen carboxylic acid or a halogen carboxylic acid derivative.
  • the halogen carboxylic acid is selected from sodium monochloroacetate, sodium 1-monochloropropionate and sodium 2-monochloropropionate.
  • the ether carboxylic acid of the invention has the following general structure: wherein the total of n + m is between 3 and 10 and preferably 6 and R is methyl, ethyl or hydrogen.
  • the ether carboxylic acid of the invention has the general structure shown in figure 1 .
  • the ether carboxylic acid of the invention has the following general structure: wherein the total of n + m is between 3 and 10 and preferably 6.
  • the ether carboxylic acid and derivative thereof according to the invention was shown to be a rheology modifier, viscosifier, lubricant and emulsifier.
  • the invention provides a lubricant composition
  • a lubricant composition comprising
  • the ether carboxylic acid or derivative thereof of the invention is a much more robust additive that effectively resists also high temperature, it can advantageously be used as an additive in a rather small amount.
  • the ether carboxylic acid or derivative thereof of the invention is present in said lubricant composition in an amount of between 0.001 wt % and 3 wt %, in a further preferred embodiment in an amount of between 0.001 wt % and 1 wt % and in another embodiment in the range from between 0.05 wt % and 0.8 wt % based on the total weight of the lubricant composition.
  • the mentioned viscosity modifier is preferably selected from the group consisting of hydrogenated copolymers of styrene-butadiene, ethylene-propylene copolymers, polyisobutenes, hydrogenated styrene-isoprene polymers, hydrogenated isoprene polymers, polymethacrylates, polyacrylates, polyalkyl styrenes, alkenyl aryl conjugated diene copolymers, polyolefins, esters of maleic anhydride-styrene copolymers, functionalized polyolefins, ethylene-propylene copolymers functionalized with the reaction product of maleic anhydride and an amine, polymethacrylate functionalized with an amine, styrenemaleic anhydride copolymers reacted with an amine, polymethacrylate polymers, esterified polymers, esterified polymers of a vinyl
  • a gel breaking surfactant is preferably selected from the group consisting of glycerol monooleate, tall oil fatty acid, linoleic and stearic acids and derivatives thereof, non-ionic surfactants, and mixtures thereof.
  • Ashless antioxidants preferably include alkyl-substituted phenols such as 2,6-di-tertiary butyl-4-methyl phenol, phenate sulfides, phosphosulfurized terpenes, sulfurized esters, aromatic amines, diphenyl amines, alkylated diphenyl amines and hindered phenols, bis-nonylated diphenylamine, nonyl diphenylamine, octyl diphenylamine, bis-octylated diphenylamine, bis-decylated diphenylamine, decyl diphenylamine and mixtures thereof.
  • alkyl-substituted phenols such as 2,6-di-tertiary butyl-4-methyl phenol, phenate sulfides, phosphosulfurized terpenes, sulfurized esters, aromatic amines, diphenyl amines, alkylated dipheny
  • Hindered phenols include but are not limited to 2,6-di-tert-butylphenol, 4-methyl-2,6-di-tert-butylphenol, 4-ethyl-2,6-di-tert-butylphenol, 4-propyl-2,6-di-tert-butyl phenol, 4-butyl-2,6-di-tert-butylphenol 2,6-di-tert-butylphenol, 4-pentyl-2-6-di-tert-butylphenol, 4-hexyl-2,6-di-tert-butylphenol, 4-heptyl-2,6-di-tert-butylphenol, 4-(2-ethylhexyl)-2,6-di-tert-butylphenol, 4-octyl-2,6-di-tert-butylphenol, 4-nonyl-2,6-di-tert-butylphenol, 4-decyl-2,6-di-
  • an ashless antioxidant is a hindered, ester-substituted phenol, which can be prepared by heating a 2,6-dialkylphenol with an acrylate ester under based conditions, such as aqueous KOH.
  • Ashless antioxidants may be used alone or in combination.
  • the antioxidants are typically present in the range of about 0 wt % to about 95 wt %, in one embodiment in the range from about 0.01 wt % to 95 wt % and in another embodiment in the range from about 1 wt % to about 70 wt % and in another embodiment in the range from about 5 wt % to about 60 wt % based on the total weight of the lubricant composition.
  • the anti-wear agents include a sulfur or chlorosulphur extreme pressure (EP) agent, a chlorinated hydrocarbon EP agent, or a phosphorus EP agent, or mixtures thereof.
  • EP agents are amine salts of phosphorus acid, chlorinated wax, organic sulfides and polysulfides, such as benzyldisulfide, bis-(chlorobenzyl) disulfide, dibutyl tetrasulfide, sulfurized sperm oil, sulfurized methyl ester of oleic acid sulfurized alkylphenol, sulfurized dipentene, sulfurized terpene, and sulfurized Diels-Alder adducts; phosphosulfurized hydrocarbons, such as the reaction product of phosphorus sulfide with turpentine or methyl oleate, phosphorus esters such as the dihydrocarbon and trihydrocarbon phosphate, i.e., dibutyl phosphate, diheptyl phosphat
  • the antiwear agent/extreme pressure agent comprises an amine salt of a phosphorus ester acid.
  • the amine salt of a phosphorus ester acid includes phosphoric acid esters and salts thereof; dialkyldithiophosphoric acid esters and salts thereof; phosphites; and phosphorus-containing carboxylic esters, ethers, and amides; and mixtures thereof.
  • the phosphorus compound further comprises a sulfur atom in the molecule.
  • the amine salt of the phosphorus compound is ashless, i.e., metal-free (prior to being mixed with other components).
  • the amines which may be suitable for use as the amine salt include primary amines, secondary amines, tertiary amines, and mixtures thereof.
  • Antifoam agents include organic silicones such as poly dimethyl siloxane, poly ethyl siloxane, polydiethyl siloxane, polyacrylates and polymethacrylates, trimethyl-triflouro-propylmethyl siloxane and the like.
  • An antifoam agent may be used in the range of about 0 wt % to about 20 wt %, in one embodiment in the range of about 0.02 wt % to about 10 wt % and in another embodiment in the range of 0.05 wt % to about 2.5 wt % based on the weight of the lubricant composition.
  • a suitable friction modifier may preferably be an organo-molybdenum compound, including molybdenum dithiocarbamate.
  • the friction modifier is a phosphate ester or salt including a monohydrocarbyl, dihydrocarbyl or a trihydrocarbyl phosphate, wherein each hydrocarbyl group is saturated.
  • Each hydrocarbyl group may contain from about 8 to about 30, or from about 12 up to about 28, or from about 14 up to about 24, or from about 14 up to about 18 carbons atoms.
  • the hydrocarbyl groups are alkyl groups.
  • hydrocarbyl groups examples include tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl groups and mixtures thereof.
  • the friction modifier is a phosphate salt
  • the phosphate salt may for example be prepared by reacting an acidic phosphate ester with an amine compound or a metallic base to form an amine or a metal salt.
  • the amines may be monoamines or polyamines.
  • the friction modifier is a phosphite and may be a monohydrocarbyl, dihydrocarbyl or a trihydrocarbyl phosphite, wherein each hydrocarbyl group is saturated.
  • each hydrocarbyl group may independently contain from about 8 to about 30, or from about 12 up to about 28, or from about 14 up to about 24, or from about 14 up to about 18 carbons atoms.
  • the hydrocarbyl groups are alkyl groups. Examples of hydrocarbyl groups include tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl groups and mixtures thereof.
  • the friction modifier is a fatty imidazoline comprising fatty substituents containing from 8 to about 30, or from about 12 to about 24 carbon atoms.
  • a suitable fatty imidazoline includes those described in U.S. Pat. No.
  • the friction modifiers can be used alone or in combination.
  • the friction reducing agents are preferably present in the range of about 0 wt % to 60 wt %, or from about 0.25 wt % to about 40 wt %, or from about 0.5 wt % to about 10 wt % based on the total weight of the lubricant composition.
  • the anti-misting agents can be used alone or in combination.
  • the anti-misting agents are present in the range of about 0 wt % to 10 wt %, or from about 0.25 wt % to about 10 wt %, or from about 0.5 wt % to about 2.5 wt % based on the total weight of the lubricant composition.
  • the corrosion inhibitors that can be used according to the invention include alkylated succinic acids and anhydrides derivatives thereof, organo phosphonates and the like.
  • the corrosion inhibitors may be used alone or in combination.
  • the rust inhibitors are present in the range of about 0 wt % to about 20 wt %, and in one embodiment in the range from about 0.0005 wt % to about 10 wt % and in another embodiment in the range from about 0.0025 wt % to about 2.5 wt % based on the total weight of the lubricant composition.
  • Demulsifiers usable in a lubricant composition of the invention include polyethylene and polypropylene oxide copolymers and the like.
  • the demulsifiers may be used alone or in combination.
  • the demulsifiers are preferably present in the range of about 0 wt % to about 20 wt %, or from about 0.0005 wt % to about 10 wt %, or from about 0.0025 wt % to about 2.5 wt % based on the total weight of the lubricant composition.
  • Said lubricity aids include glycerol mono oleate, sorbitan mono oleate and the like.
  • the lubricity aids may be used alone or in combination.
  • the lubricity aids are preferably present in the range of about 0 wt % to about 50 wt %, or from about 0.0005 wt % to about 25 wt %, or from about 0.0025 wt % to about 10 wt % based on the total weight of the lubricant composition.
  • the flow improvers mentioned in the context of the lubricant composition of the invention include ethylene vinyl acetate copolymers and the like.
  • the flow improvers may be used alone or in combination.
  • the flow improvers are preferably present in the range of about 0 wt % to about 50 wt %, or from about 0.0005 wt % to about 25 wt %, or from about 0.0025 wt % to about 5 wt % based on the total weight of the lubricant composition.
  • Said cloud point depressants include alkylphenols and derivatives thereof, ethylene vinyl acetate copolymers and the like.
  • the cloud point depressants may be used alone or in combination.
  • the cloud point depressants are preferably present in the range of about 0 wt % to about 50 wt %, or from about 0.0005 wt % to about 25 wt %, or from about 0.0025% to about 5 wt % based on the total weight of the lubricant composition.
  • the pour point depressants include alkylphenols and derivatives thereof, ethylene vinyl acetate copolymers and the like.
  • the pour point depressant may be used alone or in combination.
  • the pour point depressant are for example present in the range of about 0 wt % to about 50 wt %, or from about 0.0005 wt % to about 25 wt %, or from about 0.0025 wt % to about 5 wt % based on the total weight of the lubricant composition.
  • the seal swell agents include organo sulfur compounds such as thiophene, 3-(decyloxy)tetrahydro-1,1-dioxide, phthalates and the like.
  • the seal swell agents may be used alone or in combination.
  • the seal swell agents are for example present in the range of about 0 wt % to about 50 wt %, or from about 0.0005 wt % to about 25 wt %, or from about 0.0025 wt % to about 5 wt % based on the total weight of the lubricant composition.
  • Suitable antistatic agents include for example quaternary ammonium chlorides including alkyl benZyl ammonium chlorides and ethoxylated tertiary amine methyl ammonium chlorides; diammonium ethosulfates; ethoxylated alkyl amines (propyl to octadecyl, i.e.
  • soya and/or talloW amines such as ethoxylated amine oxides such as ethoxylated alkyl oxypropyl amine oxides (methyl to C18); trimethyl alkyl ammonium chlorides such as cetyl trimethyl ammonium chlorides; a quaternary compound Which is a reaction product of an aliphatic tertiary amine and methyl chloride; an ethoxylated amine comprising a fatty amine reacted With ethylene oxide; and an alkylated phenol such as 2,6-dibutyl-4-nonyl phenol.
  • the lubricant composition according to the invention comprises a lubricant selected from the group consisting of a paraffin, an ester, canola oil, castor oil, palm oil, sunflower seed oil, rapeseed oil, Tall oil, lanolin, olefin , polyalkylene glycol (PAG), a phosphate ester, an alkylated naphthalene (AN), a silicate ester and an ionic fluid.
  • a lubricant selected from the group consisting of a paraffin, an ester, canola oil, castor oil, palm oil, sunflower seed oil, rapeseed oil, Tall oil, lanolin, olefin , polyalkylene glycol (PAG), a phosphate ester, an alkylated naphthalene (AN), a silicate ester and an ionic fluid.
  • Drilling fluids can be used in geotechnical engineering but also in other fields.
  • a drilling fluid or mud is a specially designed fluid that is circulated through a wellbore as the wellbore is being drilled to facilitate the drilling operation. Drilling operations in general can concern oil and gas production or the generation of drilling holes useful in exploiting geothermal activity.
  • the various functions of a drilling fluid include removing drill cuttings from the wellbore, cooling and lubricating the drill bit, aiding in support of the drill pipe and drill bit, and providing a hydrostatic head to maintain the integrity of the wellbore walls and prevent well blowouts.
  • the fluid should be sufficiently viscous to suspend barite and drilled cuttings and to carry the cuttings to the well surface. However, the fluid should not be so viscous as to interfere with the drilling operation.
  • ether carboxylic acid or a derivative thereof of the invention unexpectedly was shown to be an effective rheology modifier, viscosifier, lubricant and emulsifier that can also be used in an oil drilling fluid.
  • said lubricant composition is a drilling fluid (for example used for oil or gas drilling) or a metal working fluid.
  • the lubricant composition of the invention is a water-in-oil or an oil-in-water emulsion and whereby preferably the composition comprises from 2 to 98% water and from 2 to 98% organic phase based on the volume of the lubricant composition.
  • the lubricant composition of the invention is a water-in-oil lubricant composition, i.e. comprises a continuous oil phase. If the lubricant composition of the invention is a water-in-oil lubricant composition it comprises preferably more than 50 vol% of organic phase, more preferably at least 60 vol% and most preferably at least 70 vol% of the organic phase based on the total volume of the lubricant composition.
  • the lubricant composition of the invention is an oil-in-water lubricant composition it comprises preferably more than 50 vol% of water, more preferably at least 60 vol% and most preferably at least 70 vol% of water based on the total volume of the lubricant composition.
  • Water phase as used herein means water which optionally comprises one or more dissolved water soluble compound.
  • the water is preferably present in the lubricant composition of the invention in quantities of at least about 0.5% by weight based on the weight of the emulsion. In a preferred embodiment, however, the water-in-oil lubricant composition contain between 5 and 30 wt.-% water based on the weight of the lubricant composition.
  • the water in the lubricant composition of the type described herein preferably contains electrolytes to equalize the osmotic gradient between the drilling fluid and the formation water, calcium and/or sodium salts representing the preferred electrolytes. CaCl 2 in particular may be used.
  • other salts from the group of alkali metals and/or alkaline earth metals for example potassium acetates, caesium salts, bromides (such as calciumbromide) and/or formates, are also suitable.
  • the invention relates to the use of the ether carboxylic acid or a derivative thereof of the invention as a rheology modifier, viscosifier, lubricant or emulsifier.
  • the ether carboxylic acid or a derivative thereof of the invention is used as a rheology modifier, viscosifier additive, as a lubricant additive or as an emulsifier additive for a lubricant selected from the group consisting of engine oil, oil drilling fluid, hydraulic oil, compressor oil, gear oil, bearing oil, low temperature lubricant and turbine oil.
  • ether carboxylic acids and derivatives thereof according to the invention in an oil drilling fluid leads on the one hand to stable emulsions and, on the other hand, to an improvement in the filtrate values of the drilling systems.
  • the rheology of the drilling fluid is positively influenced. It can be of advantage to use the ether carboxylic acid and derivatives thereof according to the present invention as sole emulsifier in drilling fluid systems (preferably in water-in-oil drilling fluids).
  • the ether carboxylic acid and derivatives thereof of the invention can also be combined with other ether carboxylic acids or further emulsifiers such as an emulsifier selected from the group consisting of an ether carboxylic acid ester, a fatty acid amine, an amidoamine, a fatty alcohol ethoxylate, a fatty acid ethoxylate, an alkylpolyglycoside and a fatty alcohol.
  • Emulsifiers capable of forming water in oil emulsions are preferred as further emulsifiers for this purpose.
  • ether carboxylic acids and derivatives thereof according to the invention is the use as a rheology modifier, viscosifier in oil drilling fluids.
  • FIG. 1 A general reaction scheme is shown in figure 1 .
  • a general method for producing an ether carboxylic acid of the invention is outlined.
  • the ethoxylate was mixed at 45 °C with the sodium monochloroacetate and the resulting thick suspension was stirred at 45-58 °C under N 2 for 15 minutes. NaOH was added in four portions of 11 g each and stirred each time for 45 minutes. The temperature was maintained at 56 - 58 °C. During this time the reaction was slightly exothermic only during the last hour and the mixture was getting thicker.
  • the mixture was stirred for 3 h at 70 - 77 °C while the temperature could be held mainly without active heating. Also after the addition of hydrochloric acid the mixture remained thick and was heated to 90°C while slowly stirring the composition.
  • the product was transferred to a separating funnel and kept for 30 minutes over a steam bath to separate the mixture. About 380 ml of a clear aqueous solution could be separated and was kept for 15 more minutes over the steam bath for a second round of separation. After removal of about 100 ml of aqueous phase the organic phase was dried to 104°C under water jet vacuum. About 40-50 ml water was removed this way.
  • drilling fluids with the following general composition were prepared: Ingredient / Property Amount (gram) Amount (gram) Amount (gram) Composition A B C XP 07 (paraffin) 146,3 Cross-linked polymer 1-5 CaOH 2 1-6 Terradril EM 1122 4-10 Water 77,2 CaCl 2 *2 H 2 O 40 BaSO 4 156 Hymod Prima Clay 20 C36 dimer fatty acid 0 2,5 0 Ether carboxylic acid according to example 1 0 0 2,5 Weight 457 459,5 459,5 Vol 351,9 354,4 354,4 Mud Wt, ppg 10,8 10,8 10,8 Oil/ water ratio 72/28 72/28 72/28
  • the mixing can be carried out using typical mixers well known in the art such as a Hamilton Beach or a Silverston mixer, following manufacturer's instructions.
  • the rheological characteristics including the fluids-plastic viscosity (PV), yield point (YP) and gel strength (gels 10"/10') after 10 seconds and 10 minutes were determined with a Fann Model 35A rheometer for systems A through C.
  • PV fluids-plastic viscosity
  • YP yield point
  • gel strength gels 10"/10'
  • the measuring temperature is 48.88 °C (120°F).
  • the ether carboxylic acid in system (C) shows that it acts as a viscosity increaser. Furthermore, as is evident also from the yield point values the yield point does not significantly decrease even after hot roll upon adding the ether carboxylic acid as additive. That means that the additive is also heat resistant. Also, unexpectedly, addition of the ether carboxylic acid of the invention also increases the emulsion stability as shown in the above table.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
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  • Lubricants (AREA)
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Claims (15)

  1. Acide éther-carboxylique ou dérivé de celui-ci, ledit acide éther-carboxylique pouvant être obtenu par réaction
    (a) d'un produit d'alcoxylation de polyol, pouvant être obtenu par alcoxylation d'un polyol, avec
    (b) un acide carboxylique halogéné ou un dérivé d'acide carboxylique halogéné ;
    ledit polyol étant un diol en C18-C54 ou un triol en C18-C54 ou un mélange de ceux-ci ; et ledit diol et ledit triol étant des polyols ramifiés comprenant uniquement des groupes OH primaires ;
    le dérivé étant choisi dans le groupe constitué par un sel dudit acide carboxylique, un ester dudit acide carboxylique et un amide dudit acide carboxylique.
  2. Acide éther-carboxylique ou dérivé de celui-ci selon la revendication 1, l'acide éther-carboxylique étant un acide éther-monocarboxylique, un acide éther-dicarboxylique ou un acide éther-tricarboxylique.
  3. Acide éther-carboxylique ou dérivé de celui-ci selon l'une quelconque des revendications précédentes, le diol étant un diol dimère en C36 et ledit triol étant un triol trimère en C54.
  4. Acide éther-carboxylique ou dérivé de celui-ci selon l'une quelconque des revendications précédentes, le polyol alcoxylé comprenant au total au maximum 50 radicaux alcoxy.
  5. Acide éther-carboxylique ou dérivé de celui-ci selon l'une quelconque des revendications précédentes, ledit polyol étant éthoxylé et/ou propoxylé.
  6. Acide éther-carboxylique ou dérivé de celui-ci selon l'une quelconque des revendications précédentes, le polyol étant un alcool aliphatique, comprenant éventuellement une structure cyclique, ou un alcool aromatique.
  7. Acide éther-carboxylique ou dérivé de celui-ci selon l'une quelconque des revendications précédentes, le polyol répondant à une formule générale choisie dans le groupe suivant :
    Figure imgb0034
    Figure imgb0035
    Figure imgb0036
    Figure imgb0037
    Figure imgb0038
    Figure imgb0039
    Figure imgb0040
    Figure imgb0041
     et
    Figure imgb0042
    n, o, p, q et r étant chacun individuellement choisis parmi les nombres entiers compris entre 3 et 12 ; et
    le cycle B pouvant être aromatique ou aliphatique.
  8. Acide éther-carboxylique ou dérivé de celui-ci selon la revendication 7,
    n valant 4 ou 7 ;
    o valant 5, 7 ou 8 ;
    p valant 3 ou 4 ; et
    q valant 5.
  9. Acide éther-carboxylique ou dérivé de celui-ci selon la revendication 7, ledit polyol comprenant le diol dimère suivant ou étant constitué de celui-ci :
    Figure imgb0043
  10. Acide éther-carboxylique ou dérivé de celui-ci selon l'une quelconque des revendications précédentes, l'acide carboxylique halogéné étant choisi entre le monochloroacétate de sodium, le 1-monochloropropionate de sodium et le 2-monochloropropionate de sodium.
  11. Composition de lubrifiant comprenant
    (i) un acide éther-carboxylique ou un dérivé de celui-ci tels que définis dans l'une quelconque des revendications précédentes ; et éventuellement
    (ii) un additif qui est différent dudit acide éther-carboxylique et dudit dérivé de celui-ci et qui est choisi dans le groupe constitué par un lubrifiant, un modificateur de viscosité, un modificateur de coefficient de frottement, un détergent sans cendres, un agent abaissant le point de trouble, un agent abaissant le point d'écoulement, un désémulsifiant, un agent améliorant l'écoulement, un agent antistatique, un antioxydant sans cendres, un agent antimousse, un inhibiteur de corrosion, un agent antiusure, un agent de gonflement des joints, un adjuvant améliorant le pouvoir lubrifiant, un agent antivaporisation, un solvant organique, un tensioactif de rupture de gel et les mélanges de ceux-ci.
  12. Composition de lubrifiant selon la revendication 11, ladite composition de lubrifiant comprenant un lubrifiant choisi dans le groupe constitué par une paraffine, un ester, l'huile de canola, l'huile de ricin, l'huile de palme, l'huile de tournesol, l'huile de colza, le tallöl, la lanoline, une oléfine, un polyalkylèneglycol (PAG), un ester de l'acide phosphorique, un naphtalène alkylé (AN), un ester de l'acide silicique et un fluide ionique.
  13. Composition de lubrifiant selon la revendication 11 ou 12, ladite composition de lubrifiant étant un fluide de forage de pétrole.
  14. Utilisation d'un acide éther-carboxylique ou d'un dérivé de celui-ci tels que définis dans l'une quelconque des revendications 1-10 en tant que modificateur de rhéologie, agent augmentant la viscosité, lubrifiant ou émulsifiant.
  15. Utilisation selon la revendication 14, l'acide éther-carboxylique ou un dérivé de celui-ci étant utilisés en tant que modificateur de rhéologie, additif augmentant la viscosité, en tant qu'additif lubrifiant ou en tant qu'additif émulsifiant pour un lubrifiant choisi dans le groupe constitué par une huile pour moteur, un fluide de forage de pétrole, une huile hydraulique, une huile pour compresseur, une huile pour engrenages, une huile pour roulements, un lubrifiant basse température et une huile pour turbine.
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